2-pyridylethylmercaptopyridine-n-oxides



United States Patent 2-PYRIDYLETHYLMERCAPTOPYRIDlNE-N- OXIDES Francis E. Cislak, Indianapolis, Ind., assignor to Reilly Tar & Chemical Corporation, Indianapolis, Ind., a corporation of Indiana No Drawing. Application April 18, 1957 Serial No. 653,537

4 Claims. (Cl. 260-2943) This invention relates to Z-pyridylethyhnercaptopyridine-N-oxides and to the process of making them. More particularly, it relates to 2-pyridylethylmercaptopyridine- N-oxides having the following general formula:

where R and R are hydrogen, lower alkyl, hydroxylower alkyl, or halogen; and R and R' are hydrogen or lower alkyl.

In general the compounds of my invention may be prepared by reacting a vinylpyridine with a 2-mercaptopyridine-N-oxide. The equation below portrays the preparation of 2-4'-pyridylethylmercaptopyridine-N- oxide:

+0 (1 N llI S-OHQGHH /N They may also be made by reacting a 2-halogenopyridine-N-oxide with an alkali metal salt of a mercaptoethylpyridine. The equation below portrays the preparation of 2-2-pyridylethylmercaptopyridine-N-oxide:

q fl (l (l LN 01 Na-S-CHzCH N If S-CH2OH N My invention will be described more fully in conjunction with the following specific examples. These examples are given by way of illustration only and are not to be construed as a limitation of my invention.

EXAMPLE 1 2-3'-pyridylethylmercaptopyridine-N-oxide @S-CEMCH An aqueous solution of 40 grams of the sodium salt of B-mercaptoethylpyridine is warmed to a temperature of about 50 C. While stirring this solution, there is added to it, in small portions, 50 grams of 2-bromopyridine-N-oxide. After all of the latter has been added, the

r 2,826,585 Patented Mar. 11, 1958 reaction mixture is heated for about another hour at a temperature of from about 50 C. to C. Then there is added about 5 to 10 grams of decolorizing carbon, and the mixture is hot filtered. The filtrate is cooled to about 15-25 C. and made acid (pH 1.7) with hydrochloric acid. The 2-3-pyridylethylmercaptopyridine-N- oxide is recovered in any convenient manner, recrystallized from alcohol, and dried.

EXAMPLE 2 2-2-5-ethylpyridylethylmercapto-S-methylpyridine- N-pxide The procedure of Example 1 is repeated with the exception that 2-mercaptoethyl-S-ethylpyridine is used in place of 3-mercaptoethylpyridine and 2-bromo-5-methylpyridine-N-oxide is used in place of the Z-bromopyridine- N-oxide.

EXAMPLE 3 2-4 '-pyridylezhylmercaptopyridine-N-oxide S- H N/ 0 The procedure of Example 1 is repeated with the exception that 4-mercaptoethylpyridine is used] in place of the B-mercaptoethylpyridine.

EXAMPLE 4 2 2' 4',6 dimethylpyridylethylmercaptopyridine N-oxide CH; @S-CIMOHQCH:

The procedure of Example 1 is repeated with the exception that 2-mercaptoethyl-4,6-dimethylpyridine is used in place of the 3-mercaptoethylpyridine.

EXAMPLE 5 2 2'-pyridyIethylmercapt0-5-brom0pyridine-N-0xide N/ S-CHr-CH N/ e 3 EXAMPLE 6 2-3'-6'-methylpyridylethylmercaptopyridine-N-oxide S-CHaOH CH: N

The procedure of Example 1 is repeated with the exception that 3-mercaptoethyl-6-methylpyridine is used in place of 3-mercaptoethylpyridine.

My 2-pyridylethylmercaptopyridine-N-oxides are useful as inhibitors in the pickling of steel with nonoxidizing mineral acids.

The compounds of this invention possess bactericidal and fungicidal properties. 'A'solution of 2-4-pyridylethylmercaptopyridine-N-oxide in 4-nonylpyridine has pronounced fungicidal properties. Quaternary ammonium salts of my compounds are useful as disinfecting and sterilizing agents.

4 I claim as my invention. 1. 2-pyridylethylmercaptopyridine-N-oxides having the following general formula:

B-CHaCH wherein R and R are selected from the group consisting of hydrogen, lower alkyl, hydroxy-lower alkyl, and halogen; R and R are selected from the group consisting of hydrogen and lower alkyl.

2. 2-4'-pyridylethylmercaptopyridine-N-oxide.

3. 2-2'-pyridylethylmercaptopyridine-N-oxide.

4. 2 3 6 methylpyridylethylmercaptopyridine N-oxide.

No references cited. 

1. 2-PYRIDYLETHYLMERCAPTOPYRIDINE-N-OXIDES HAVING THE FOLLOWING GENERAL FORMULA: 